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Novel pathways of interaction of maleic anhydride derivatives with phosphorus(III) compounds: synthesis and characterisation of N,N,N′,N′-tetraethyl-2,3-diphenylbut-2-enediamide and 3-dihydrofuranylidene-4-phosphorylidene-oxolane-2,5,5′-trione

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Abstract

Maleic anhydride undergoes C-phosphorylation under the action of tris(diethylamino)phosphine to afford 3-dihydrofuranylidene-4-phosphorylidene-oxolane-2,5,5′-trione whereas 2,3-diphenylmaleic anhydride under the same conditions turns into N,N,N′,N′-tetraethyl-2,3-diphenylbut-2-enediamide. The latter reaction can serve as a novel approach for the synthesis of dicarboxylic acids diamides from corresponding cyclic anhydrides. Their structures were established by NMR and X-ray diffraction.

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References

  • Bird, C. W., & Wong, D. Y. (1969). The deoxygenative dimerisation of carboxylic anhydrides. Journal of the Chemical Society D: Chemical Communications, 1969 932–932. DOI: 10.1039/c29690000932.

    Article  Google Scholar 

  • Fañanás, F. J., & Hoberg, H. (1984). Durch nickel(II)-salze induzierte carbamoylierung von alkinen. Journal of Organometallic Chemistry, 277 135–142. DOI: 10.1016/0022-328x(84)80688-9.

    Article  Google Scholar 

  • Gallagher, M. J., & Jenkins, I. D. (1969). Organophosphorus intermediates. Part II. Reaction of tervalent phosphorus compounds with tetraphenylcyclopentadienone. Journal of the Chemical Society C: Organic 2605–2614. DOI: 10.1039/j39690002605.

  • Holm, R. H. (1987). Metal-centered oxygen atom transfer reactions. Chemical Reviews, 87 1401–1449. DOI: 10.1021/cr00082a005.

    Article  CAS  Google Scholar 

  • Hudson, R. F., & Chopard, P. A. (1963). Structure et réactions du composé d’addition: triphénylphosphine — anhydride maléique. Helvetica Chimica Acta, 46 2178–2185. DOI: 10.1002/hlca.19630460638.

    Article  CAS  Google Scholar 

  • Markgraf, J. H., Heller, C. I., & Avery, N. L., III. (1970). The reaction of thiophthalic anhydride with trivalent phosphorus. The Journal of Organic Chemistry, 35 1588–1591. DOI: 10.1021/jo00830a069.

    Article  CAS  Google Scholar 

  • Osuch, C., Franz, J. E., & Zienty, F. B. (1964). The adduct of triphenylphosphine and maleic anhydride. The Journal of Organic Chemistry, 29 3721–3722. DOI: 10.1021/jo01035a522.

    Article  CAS  Google Scholar 

  • Ramirez, F., Yamanaka, H., & Basedow, O. H. (1961). Newreactions of phosphite esters: the conversion of phthalic anhydride into biphthalyl by trialkyl phosphites and into phthalide-3-phosphonates by dialkyl phosphites. Journal of the American Chemical Society, 83 173–178. DOI: 10.1021/ja01462a034.

    Article  CAS  Google Scholar 

  • Schönberg, A., & Ismail, A. F. A. (1940). A colour reaction of maleic anhydride, p-benzoquinone, their partially substituted derivatives, and citric acid. Some zwitterions. Journal of the Chemical Society, 1940 1374–1378. DOI: 10.1039/jr9400001374.

    Article  Google Scholar 

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Correspondence to Andrei V. Bogdanov.

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Musin, L.I., Bogdanov, A.V., Krivolapov, D.B. et al. Novel pathways of interaction of maleic anhydride derivatives with phosphorus(III) compounds: synthesis and characterisation of N,N,N′,N′-tetraethyl-2,3-diphenylbut-2-enediamide and 3-dihydrofuranylidene-4-phosphorylidene-oxolane-2,5,5′-trione. Chem. Pap. 69, 1012–1015 (2015). https://doi.org/10.1515/chempap-2015-0094

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  • DOI: https://doi.org/10.1515/chempap-2015-0094

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